Oil composition

ABSTRACT

Disclosed herein is an oil composition comprising the following components (A) and (B):(A) 15 to 70% by weight of diglycerides in which less than 15% by weight of the constitutive fatty acids are (3 type unsaturated fatty acids; and (B) 30 to 85% by weight of a triglyceride in which at least 15% by weight of the constitutive fatty acids are (3 type unsaturated fatty acids. The oil composition is good in flavor, hard to be colored, excellent in hydrolytic stability and resistance to oxidation, good in emulsion stability and excellent in intake balance among fatty acids even under severe conditions that heating is performed at a high temperature for a long period of time, can be widely developed to medicinal preparations and foods and moreover exhibit an excellent inhibitory effect on accumulation of body fat by ingestion of a small amount of diglycerides.

BACKGROUND OF THE INVENTION

[0001] 1. Field of the Invention

[0002] The present invention relates to an oil or fat (hereafterreferred to as “oil” merely) composition which is good in flavor, hardto be colored and high in hydrolysis stability, oxidation stability andemulsion stability even under severe conditions that heating isperformed at a high temperature for a long period of time and thus canbe used in various kinds of pharmaceutical preparations, foods and feedsand moreover has an excellent inhibitory effect on accumulation of bodyfat.

[0003] 2. Related Background Art

[0004] In recent years, researches on the relationship betweendistribution of body fat and various life-style related diseases havebeen advanced. In particular, it has been shown that the accumulation ofvisceral fats such as intraperitoneal fat and hepatic fat has highcorrelation with diabetes, hyperlipidemia, hepatic diseases,hypertension, etc., to say nothing of obesity. It is accordinglyimportant from the viewpoint of preventing and treating these diseasesto reduce the body fat.

[0005] Techniques of using diglycerides as edible oils have been alreadydisclosed (Japanese Patent Application Laid-Open No. 7-16053, U.S. Pat.No. 4,656,045, EP 0525915 and WO 96/32022, etc.), and it has been foundthat diglycerides have an effect to reduce the accumulation of body fatto prevent obesity (Japanese Patent Application Laid-Open No. 4-300828and U.S. Pat. No. 6,004,611, etc.). The diglycerides are considered toinhibit increase of neutral lipid in blood, thereby reducing theaccumulation of body fat.

[0006] However, a diglyceride is hydrolyzed and oxidized by heating orstorage for a long period of time like triglycerides. The smoke point ofthe diglyceride is lowered by the influence of a fatty acid liberated bythe hydrolysis to cause problems on smell during cooking andoperability. In addition, problems of production of odor bydeterioration, coloring, deterioration of flavor, etc. are also causedby the oxidation.

[0007] There is no extremely useful prior art for a method for improvingthe hydrolytic stability of an oil (triglyceride). On the other hand, astechniques for preventing oxidation, there have been proposed a methodof adding any of various kinds of antioxidant to an oil for frying and amethod of adding citric acid as a synergist (Theory and Practice ofFried Food, edited by Saiwai Shobo, 1976). However, in the latter methodin particular, citric acid or a salt thereof is hardly soluble in oils,and so its effect has not been sufficient (Japanese Patent ApplicationLaid-Open No. 49-86557).

[0008] On the other hand, triglycerides, particularly, triglyceridescontaining ω3 type unsaturated fatty acid(s) have been known to havephysiological effects, for example, an antiallergic effect (JapanesePatent Application Laid-Open No. 63-36744) and an effect of preventingdiseases of the circulatory system (Japanese Patent ApplicationLaid-Open No. 61-85143). On the basis of such properties, application tofoods and drinks for infants and patients of allergic diseases has beenproposed (Japanese Patent Application Laid-Open No. 9-121766).

[0009] However, such highly unsaturated fatty acid-containingtriglycerides are very easy to be oxidized. In Japanese PatentApplication Laid-Open Nos. 4-46998 and 8-116878, etc., applications ofthese triglycerides to edible oils have been proposed. However,oxidation stability has not been sufficient. In order to solve such aproblem, an addition of a great amount of an antioxidant has been knownas a method for preventing the oxidation of triglycerides. However,antioxidants greatly soluble in a triglyceride are few, and there is alimit to use. In addition, the antioxidant effect of the fewantioxidants is not sufficient even when they are used in a greatamount. As another method for preventing the oxidation, powdering(Japanese Patent Application Laid-Open Nos. 9-121766 and 7-313057) orthe like has been conducted. However, it has been difficult to widen avariation as a preparation. As described above, any technique for widelyhandling the triglycerides containing the highly unsaturated fattyacid(s) has not been yet established under the circumstances.

[0010] With respect to the oxidation stability of the highly unsaturatedfatty acid-containing triglycerides and the diglycerides, there is aparticularly strong demand for improvement in institutional orprocessing oils used under particularly severe conditions in fry works,daily dish shops, eating houses, restaurants, etc. Ascorbyl palmitate,tocopherol or the like may be used as an antioxidant in an increasedamount in some cases. However, its effect is not sufficient. Withrespect to oils, there are problems of increase in smoke attendant onrise of acidic value, appearance discoloration and the like duringcooking. With respect to fried products, there are problems ofdeterioration of flavor, color tone and/or appearance, and the like dueto soap odor or the like based on decomposed fatty acids. Morespecifically, the diglycerides have a unique effect of inhibiting theaccumulation of body fat and on one hand involve a problem that theiruses are limited according to service conditions. On the other hand, inthe highly unsaturated fatty acid-containing triglycerides, any solutionto sole use at a high temperature has not been yet found from theviewpoints of oxidation stability and flavor. In addition, any techniquefor widely handling the highly unsaturated fatty acid-containingtriglycerides has not be yet established due to great restrictions onpreparations.

SUMMARY OF THE INVENTION

[0011] It is therefore an object of the present invention to provide anoil composition which is good in flavor, hard to be colored andexcellent in hydrolysis stability, resistance to oxidation and emulsionstability even under severe conditions that heating is performed at ahigh temperature for a long period of time, can be widely developed topharmaceutical preparations, foods and feeds and moreover has anexcellent inhibitory effect on accumulation of body fat.

[0012] The present inventors have found that when the contents ofdiglycerides and a triglyceride in an oil composition and the contentsof specific unsaturated fatty acids in fatty acids constituting suchglycerides are varied, the amount of an antioxidant dissolved in the oilcomposition is increased, and the oil composition can be provided as anoil composition which is good in flavor, hard to be colored, excellentin hydrolysis stability and resistance to oxidation, good in emulsionstability and excellent in intake balance among fatty acids even undersevere conditions that heating is performed at a high temperature for along period of time, can be widely developed to pharmaceuticalpreparations and foods and moreover has an excellent inhibitory effecton accumulation of body fat, and also that this oil composition isexcellent in the effect of inhibiting the accumulation of body fat evenwhen the content of the diglycerides is lower than the conventionaldiglyceride-containing oil composition (U.S. Pat. No. 6,004,611).

[0013] According to the present invention, there is thus provided an oilcomposition comprising the following components (A) and (B):

[0014] (A) 15 to 70% by weight of diglycerides in which less than 15% byweight of the constitutive fatty acids are ω3 type unsaturated fattyacids; and

[0015] (B) 30 to 85% by weight of a triglyceride in which at least 15%by weight of the constitutive fatty acids are ω3 type unsaturated fattyacids.

[0016] According to the present invention, there is also provided afood, feed or pharmaceutical comprising such an oil composition.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The oil composition according to the present invention comprises15 to 70% by weight (hereafter indicated merely by “%”) of diglyceridesas the component (A) in which less than 15% of the constitutive fattyacids are ω3 type unsaturated fatty acids. From the viewpoints of thestability, physiological effect and emulsion stability of the oil, thecontent of the diglycerides is preferably 20 to 59.9%, more preferably30 to 49.9%, particularly preferably 35 to 49.9%. Although thediglycerides include 1,3-diglyceride and 1,2-diglyceride, the1,3-diglyceride is preferred from the viewpoint of the physiologicaleffect. It is desirable from the viewpoints of the physiological effect,stability of the oil and industrial productivity that the content of the1,3-diglyceride in the oil composition be 9 to 55%, preferably 12 to50%, more preferably 16 to 40%, particularly preferably 20 to 39%.

[0018] The term “ω3 type unsaturated fatty acid” as used herein means afatty acid that a first carbon-carbon double bond is located on thethird carbon atom from an (o position, and that has at least 2carbon-carbon double bonds. Examples thereof include unsaturated fattyacids having 14 to 19 carbon atoms, such as α-linolenic acid andstearidonic acid and unsaturated fatty acids having 20 to 30 carbonatoms, such as eicosapentaenoic acid, docosapentaenoic acid anddocosahexaenoic acid, with α-linolenic acid being particularlypreferred. The ω3 type unsaturated fatty acids are desirably containedin a proportion of preferably 0 to 14.9%, more preferably 0.1 to 14%,still more preferably 0.5 to 12%, particularly preferably 1 to 10%, mostpreferably 4 to 10%, in the constitutive fatty acids of the diglyceridesfrom the viewpoint of the stability and physiological effect of the oil.

[0019] It is preferred from the viewpoints of oxidation stability andintake balance among fatty acids that an ω9 type unsaturated fatty acidbe contained as a residual constitutive fatty acid of the diglyceridesin a proportion of 1 to 70%, preferably 5 to 60%, more preferably 10 to50%, particularly preferably 20 to 45%. Examples of the ω9 typeunsaturated fatty acid include unsaturated fatty acids having 10 to 24carbon atoms, preferably 16 to 22 carbon atoms, such as oleic acid,eicosamonoenoic acid and docosamonoenoic acid, with oleic acid beingparticularly preferred. From the viewpoint of development of thephysiological effect, the olein-olein diglyceride content is preferablylower than 45%, more preferably 0 to 40%.

[0020] It is preferred from the viewpoints of oxidation stability,intake balance among fatty acids and development of physiologicalactivity effect derived from the ω3 type unsaturated fatty acids that anω6 type unsaturated fatty acid having 18 to 22 carbon atoms, such aslinoleic acid or γ-linolenic acid be contained as a further constitutivefatty acid of the diglycerides in a proportion of 2 to 80%, preferably 5to 70%, more preferably 10 to 60%, particularly preferably 20 to 50%. Itis desirable from the oxidation stability and development ofphysiological activity effect that a weight ratio of linoleic acid tooleic acid contained be 0.01 to 2.0, preferably 0.1 to 1.8, particularly0.3 to 1.7.

[0021] It is preferred from the viewpoints of the development ofphysiological activity and industrial productivity that 55 to 100%,preferably 70 to 100%, more preferably 80 to 100, particularlypreferably 90 to 100% of the constitutive fatty acids of thediglycerides be unsaturated fatty acids having 10 to 24 carbon atoms,particularly preferably unsaturated fatty acids having 16 to 22 carbonatoms. The residual constitutive saturated fatty acids preferably have14 to 24 carbon atoms, preferably 16 to 22 carbon atoms.

[0022] The diglycerides can be obtained by an optional process such astransesterification of an oil with glycerol or esterification of a fattyacid derived from an oil with glycerol. The reaction method thereof maybe either a chemical reaction method making use of an alkali catalyst orthe like or a biochemical reaction method making use of a lipolyticenzyme such as lipase.

[0023] Examples of the oil include vegetable oils such as soybean oil,rapeseed oil, palm oil, rice oil, corn oil, sunflower oil, saffloweroil, olive oil and sesame oil; animal oils such as beef tallow, lard andfish oil; and hardened oils, fractionated oils, transesterified oils andrandom transesterified oils thereof.

[0024] The oil composition according to the present invention comprises30 to 85% of a triglyceride as the component (B) in which at least 15%of the constitutive fatty acids are ω3 type unsaturated fatty acids. Itis desirable from the viewpoints of the stability, physiological effectand emulsion stability of the oil that the content of the triglyceridebe preferably 40 to 79.9%, particularly 50 to 69.9%. Examples of the ω3type unsaturated fatty acids include unsaturated fatty acids having 14to 19 carbon atoms, such as α-linolenic acid and stearidonic acid andunsaturated fatty acids having 20 to 30 carbon atoms, such aseicosapentaenoic acid, docosapentaenoic acid and docosahexaenoic acid,with α-linolenic acid being particularly preferred. The ω3 typeunsaturated fatty acids are desirably contained in a proportion of 15 to90%, preferably 17 to 60%, more preferably 17 to 40%, particularlypreferably 20 to 30% in the constitutive fatty acids of the triglyceridefrom the viewpoint of the stability and physiological effect of the oil.The content of α-linolenic acid in the ω3 type unsaturated fatty acidsis preferably at least 50%, more preferably 70 to 100%, particularlypreferably 90 to 100%.

[0025] It is desirable from the viewpoints of oxidation stability andintake balance among fatty acids that an o)9 type unsaturated fatty acidbe contained as a residual constitutive fatty acid of the triglyceridein a proportion of 1 to 80%, preferably 5 to 70%, more preferably 10 to60%, particularly preferably 20 to 50%. Examples of the ω9 typeunsaturated fatty acid include unsaturated fatty acids having 10 to 24carbon atoms, preferably 16 to 22 carbon atoms, such as oleic acid,eicosamonoenoic acid and docosamonoenoic acid, with oleic acid beingparticularly preferred.

[0026] It is preferred from the viewpoints of intake balance among fattyacids and development of physiological activity effect derived from theω3 type unsaturated fatty acids that an ω6 type unsaturated fatty acidhaving 18 to 22 carbon atoms, such as linoleic acid or γ-linolenic acidbe contained as a further constitutive fatty acid of the triglyceride ina proportion of 1 to 60%, preferably 2 to 50%, more preferably 5 to 40%,particularly preferably 10 to 30%.

[0027] It is preferred from the viewpoints of the development ofphysiological activity that 40 to 100%, preferably 55 to 100%, morepreferably 70 to 100, particularly preferably 80 to 100% of theconstitutive fatty acids of the triglyceride be unsaturated fatty acidshaving 12 to 24 carbon atoms, preferably unsaturated fatty acids having16 to 22 carbon atoms. The residual constitutive saturated fatty acidspreferably have 14 to 24 carbon atoms, preferably 16 to 22 carbon atoms.

[0028] As such a triglyceride, may be used an oil such as perilla oil,linseed oil, wax tree kernel oil or fish oil, and it is prepared byesterification of a ω3 type unsaturated fatty acid such as α-linolenicacid with glycerol, or the like. The reaction method thereof may beeither a chemical reaction method making use of an alkali catalyst orthe like or a biochemical reaction method making use of a lipolyticenzyme such as lipase.

[0029] The constitutive fatty acids in the triglyceride can be preparedby mixing or transefterifying the above-described oil containing the ω3type unsaturated fatty acids as constitutive unsaturated fatty acidswith another oil such as rapeseed oil, soybean oil, sunflower oil,safflower oil, olive oil, sesame oil, corn oil or cotton-seed oil. Thetriglyceride used herein may be liquid or solid at normal temperature.

[0030] The residual components of the oil composition according to thepresent invention are a monoglyceride, free fatty acids and the like.The monoglyceride is desirably contained in a proportion of 0 to 10%,preferably 0.1 to 10%, more preferably 0.1 to 5%, still more preferably0.1 to 1.5%, particularly preferably 0.1 to 1% in the oil compositionfrom the viewpoints of prevention of smoking upon heating, flavor,industrial productivity, emulsification, etc. The content of the freefatty acids (salts) is preferably reduced to at most 3.5%, morepreferably 0 to 2.5%, still more preferably 0 to 1.5%, particularlypreferably 0 to 1%, most preferably 0 to 0.5% from the viewpoints ofprevention of smoking upon heating and flavor.

[0031] The content of fatty acids having at least 4 carbon-carbon doublebonds in all the constitutive fatty acids in the oil compositionaccording to the present invention is preferably 0 to 40%, morepreferably 0 to 20%, still more preferably 0 to 10%, particularlypreferably 0 to 1% from the viewpoints of physiological effect,oxidation stability, coloring, etc., and such fatty acids are mostpreferably substantially not contained.

[0032] An antioxidant is preferably added in a proportion of 0.004 to5%, more preferably 0.004 to 2%, particularly preferably 0.02 to 1% tothe oil composition according to the present invention from theviewpoints of oxidation stability, coloring, etc. Any antioxidant may beadded so far as it is commonly used in foods, pharmaceuticals and feeds.However, a natural antioxidant, phospholipid, catechin, BHT(dibutylhydroxytoluene), BHA (butylhydroxyanisole), TBHQ(tert-butylhydroquinone), propyl gallate, L-proline, rosemary extract,vitamin C or a derivative thereof, or vitamin E is preferred from theviewpoint of antioxidant property. Two or more of these antioxidants maybe used in combination. For example, rosemary extract and vitamin C or aderivative thereof, or vitamin C or a derivative thereof and vitamin Eare preferably contained in combination. Rosemary extract, vitamin C ora derivative thereof and vitamin E are particularly preferably containedin combination.

[0033] The rosemary extract is an extract products by drying andgrinding leaves of rosemary which is a plant of Lamiaceae, andextracting them with water, hot water, hexane, ethanol, acetone, ethylacetate or a mixed solvent thereof. In the present invention, besidesthe above-described extracts with the organic solvent, oleo-resinpreparations prepared from this extract, or preparations of rosemanol,calsonol, isorosmarol, etc. which are constituents thereof may also beused. Products (hereinafter referred to as deodorized products) obtainedby subjecting these extracts to a deodorizing treatment by a methodunder reduced pressure, a method under heating and reduced pressure, asupercritical extraction method, a column adsorption method or the likeare particularly preferred from the viewpoint of flavor. The amount of asolvent remaining in these deodorized products is preferably at most 20ppm, particularly preferably at most 15 ppm. Examples of commerciallyavailable rosemary extracts include Herbalox Type O, Herbalox Type HT-O,Herbalox Type 25, Duolite NMH and Duolite NM-1 (all, products of KalsecCo.), and Leomi-ru E and Leomi-ru IO (both, product of LionCorporation).

[0034] The content of these rosemary extracts in the oil compositionaccording to the present invention is preferably 0.02 to 0.5%, morepreferably 0.05 to 0.35%, particularly preferably 0.1 to 0.3% in termsof dewatered and desolvated products from the viewpoint of impartinggood antioxidant property to the oil composition.

[0035] Examples of vitamin C or the derivative thereof includeL-ascorbic acid fatty acid esters.

[0036] The L-ascorbic acid fatty acid esters are preferably thosedissolved in the diglyceride-containing oil composition, more preferablyhigher fatty acid esters the number of carbon atoms of the acyl group inwhich is 12 to 22, particularly preferably L-ascorbyl palmitate orL-ascorbyl stearate, most preferably L-ascorbyl palmitate.

[0037] The content of vitamin C or the derivative thereof in the oilcomposition according to the present invention is preferably at least0.004%, more preferably 0.006 to 0.08%, particularly preferably 0.008 to0.06% in terms of ascorbic acid from the viewpoint of imparting goodantioxidant property to the oil composition.

[0038] As vitamin E, is used α-, β-, γ- or δ-tocopherol or a mixturethereof, with 6-tocopherol being particularly preferred from heatresistance. Examples of commercially available vitamin E productsinclude E Mix D and E Mix 80 (both, products of Eisai Co., Ltd.),MDE-6000 (product of Yashiro Co., Ltd.), and E Oil-400 (product of RikenVitamin Co., Ltd.).

[0039] The content of vitamin E in the oil composition according to thepresent invention is preferably at least 0.01%, more preferably 0.02 to0.4%, particularly preferably 0.05 to 0.3% in terms of tocopherol fromthe viewpoint of imparting good antioxidant property to the oilcomposition.

[0040] When an organic carboxylic acid having 2 to 8 carbon atoms, suchas a hydroxycarboxylic acid, dicarboxylic acid or tricarboxylic acid, ora salt thereof is contained in the oil composition according to thepresent invention, hydrolysis is more inhibited. It is hence preferableto contain such a compound. Specific preferable examples thereof includecitric acid, succinic acid, maleic acid, oxalic acid, aconitic acid,itaconic acid, citraconic acid, tartaric acid, fumaric acid and malicacid. Citric acid, tartaric acid and malic acid are more preferred.Examples of commercially available citric acid products include citricacid (crystal) monoglyceride (product of ADM Co.) and purified citricacid crystal monoglyceride (product of Fuso Chemical Industries Co.,Ltd.). Examples of salts of the organic carboxylic acids include alkalimetal salts and alkaline earth metal salts thereof, with the sodiumsalts and calcium salts being preferred.

[0041] As the organic carboxylic acid, may be used an extract or crudedrug containing the organic carboxylic acid. The extract or crude drugmay be used as a product in the form of powder, concentrate or the like,which is prepared by extracting fruits of lemon, citron, Japaneseapricot and commercially available.

[0042] The content of the organic carboxylic acid or the salt thereof inthe oil composition according to the present invention is at least0.001%, preferably 0.001 to 0.2%, more preferably 0.0015 to 0.15%,particularly preferably 0.002 to 0.1% from the viewpoint of the effectof inhibiting hydrolysis. When the extract or crude drug is used, it isonly necessary to add it in such a manner that the amount of the organiccarboxylic acid contained in the extract or crude drug falls within theabove range.

[0043] It is preferred from the viewpoint of antifoaming property that asilicone be further contained in the oil composition according to thepresent invention in addition to the antioxidant.

[0044] Examples of the silicone include preparations (KS-66, KS-69,KF-96, KM-72, etc., all products of Shin-Etsu Chemical Co., Ltd.;THF450, TSA737, etc., all products of Toshiba Silicone Co., Ltd.) knownas antifoaming agents for food, such as dimethyl polysiloxane. Theoxidation stability of the oil composition according to the presentinvention is still more improved by containing the silicone in thecomposition, and the deterioration of flavor upon use of the oilcomposition is also improved.

[0045] The content of the silicone in the oil composition according tothe present invention is preferably at least 0.3 ppm, more preferably0.5 to 10 ppm, particularly preferably 1 to 10 ppm.

[0046] The oil composition according to the present invention can beobtained by optionally adding the organic carboxylic acid, the rosemaryextract, vitamin C or the derivative thereof, vitamin E, the silicone,etc. to the diglyceride-containing oil of the above-describedcomposition and suitably heating and stirring the resultant mixture. Therosemary extract, vitamin C derivative, vitamin E and the like may alsobe dissolved in a solvent such as ethanol in advance before the additionthereof.

[0047] The oil composition according to the present invention is stableto long-time heating and storage and useful as, for example, an edibleoil. The oil composition according to the present invention is alsouseful as an antioxidant that can improve the oxidation stability of anordinary edible oil by adding it to the edible oil.

[0048] The oil composition according to the present invention preferablyfurther comprises phytosterol. The phytosterol is a component having acholesterol-reducing effect. The content of the phytosterol in the oilcomposition according to the present invention is preferably at least0.05%, particularly at least 0.3%. The content of phytosterol in acommonly sold oil composition prepared using, as a raw material, a fattyacid obtained by distillation is reduced. In such a case, thephytosterol may preferably be added in such a manner that the contentthereof amounts to at least 0.05%, and preferably falls within a rangeof 0.05 to 1.2%. When it is intended to reduce cholesterol to a greaterextent than ordinary plant oils, the phytosterol may also be added in anamount of 1.2 to 20%, preferably 1.2 to 4.5%. Examples of thephytosterol used in the present invention include free substances suchas α-sitosterol, β-sitosterol, stigmasterol, campesterol, α-sitostanol,β-sitostanol, stigmastanol, campestanol and cycloartenol, and besidesesters thereof, such as fatty acid esters, ferulic acid esters andcinnamic acid esters.

[0049] The oil composition according to the present invention preferablyfurther comprises a crystallization inhibitor.

[0050] Examples of crystallization inhibitors used in the presentinvention include polyol fatty acid esters such as polyglycerolcondensed ricinoleic acid esters, polyglycerol fatty acid esters,sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylenesorbitan fatty acid esters and propylene glycol fatty acid esters.

[0051] Among these polyol fatty acid esters, polyglycerol fatty acidesters, sucrose fatty acid esters, sorbitan fatty acid esters whose HLB(Griffin's equation, J. Soc. Cosmet. Chem., 1, 311 (1949)) is at most 4,particularly at most 3 are preferred.

[0052] The crystallization inhibitor is preferably contained in aproportion of 0.02 to 2%, preferably 0.02 to 0.5%, particularlypreferably 0.05 to 0.2% in the oil composition according to the presentinvention from the viewpoint of improving stability at a lowtemperature.

[0053] The oil composition according to the present invention hasexcellent physiological activities such as effects of inhibitingaccumulation of body fat, inhibiting increase of serum triglycerides,inhibiting increase of chylomicron triglycerides, inhibitingaccumulation of visceral fats, inhibiting increase of body weight,inhibiting rise of blood sugar and improving insulin resistance. Inaddition, since it is good in flavor, hard to be colored and high inhydrolytic stability and the like even under severe conditions thatheating is performed at a high temperature for a long period of time,and thus excellent in suitability for frying, its uses are not limited.Since the oil composition according to the present invention has suchexcellent properties, it can be used in foods, feeds and pharmaceuticalsin the form of an oil-in-water type emulsion, water-in-oil typeemulsion, capsule, tablet, granule, powder, gel, pellet, oil or thelike.

[0054] With respect to the foods, the oil composition can be used asprocessed oil foods containing the oil composition as a part of food.Examples of such processed oil-containing foods include healthy foods,functional foods and specified healthy foods that the specifiedfunctions are exhibited to promote health. Examples of specific productsthereof include bakery foods such as bread, cakes, biscuits, pies, pizzacrusts and bakery mixes; oil-in-water type emulsions such as soup,sauce, dressings, mayonnaises, coffee whiteners, ice creams and whippedcreams; water-in-oil type emulsions such as margarine, margarine-likespreads and butter creams; snack confectionery such as potato chips;confectionery such as chocolate, caramels, candies and desserts;processed meat products such as ham, sausage and Hamburg steak; dairyproducts such as milk, cheese and yogurt; and frying shortening, bakingshortening, dough, enrober oils, filling oils, noodles, frozen foods,retort foods, drinks and roux. Such processed oil food can be producedby adding food materials commonly used according to the kind of theprocessed oil food in addition to the oil composition. It is preferredthat the amount of the oil composition according to the presentinvention to be incorporated in food be generally 0.1 to 100%,particularly 1 to 80% though it varies according to the kind of thefood. It may also be used as a food material of a cooking oil or thelike used for fried food or frizzled food. In particular, it is suitablefor use in cooking daily dish such as croquette, tempura, pork cutlet,food fried without coat, fried fishes and harumaki (spring roll); snackconfectionery such as potato chips, tortilla chips and fabricatedpotato; fried confectionery such as fried Japanese cracker (age senbei);and fried potato, fried chicken, doughnut and instant noodle.

[0055] When an oil derived from a food material is contained because ofnecessity for preparation of a product, a Weight ratio of the oilderived from the food material to the oil composition according to thepresent invention is preferably 95:5 to 1:99, more preferably 95:5 to5:95, still more preferably 85:15 to 5:95, particularly preferably 40:60to 5:95.

[0056] The oil composition according to the present invention can beused in a pharmaceutical. Examples of the pharmaceuticals include oralpreparations such as solid preparations, liquid preparations and gelpreparations. Such an oral preparation can be prepared by adding anexcipient, a disintegrator, a binder, a lubricant, a surfactant, analcohol, water, a water-soluble polymer, an edulcorant, a tastecorrigent, an acid corrigent and/or the like commonly used according tothe form of the oral preparation in addition to the oil composition. Itis preferred that the amount of the oil composition according to thepresent invention to be incorporated in the oral preparation begenerally 0.1 to 80%, particularly 0.2 to 50% though it varies accordingto the application and form of the medicine. With respect to the dose ofthe oil composition as a medicament, it is-preferably administered in adose of 0.2 to 50 g per day. Meanwhile, the administration may be onceper day, or may be divided into several times per day.

[0057] The oil composition according to the present invention can beused in a feed. Examples of the feeds include feeds for livestock usedin cattle, swine, fowl, sheep, horseflesh, etc., feeds for small animalsused in rabbit, rats, mice, etc., feeds for fishes and shellfishes usedin eels, sea breams, young yellowtails, lobsters, etc., and pet foodsused in dogs, cats, small birds, squirrels, etc. It is preferred thatthe amount of the oil composition according to the present invention tobe incorporated in the feed be generally 1 to 30%, particularly 1 to 20%though it varies according to the application of the feed. The oilcomposition according to the present invention may be used by replacingthe whole or a part of an oil in a feed by it.

[0058] The feed can be produced by mixing feed materials commonly used,such as meat, proteins, cereals, brans, meals, saccharides, vegetables,vitamins and minerals, with the oil composition. Examples of the meatinclude meat or game of cattle, swine, sheep (mutton or ram), rabbit,kangaroo, etc., and by-products and processed products thereof;rendering products of the above-mentioned raw materials, such asmeatball, meat-bone meal and chicken meal; and fish and fish meal oftuna, bonito, bluefish, sardine, scallop, turbo, etc. Examples of theproteins include milk proteins such as casein whey, and plant proteinssuch as soybean protein, the cereals include wheat, barley, rye, miloand corn. Examples of the brans include rice bran and wheat bran.Examples of the meals include soybean meal. The total amount of themeat, proteins, cereals, brans and meals in the feed is preferably 5 to95%. Examples of the saccharides include glucose, oligosaccharides,sugar, molasses, starch and syrup, and the they are preferably containedin an amount of 5 to 80% in the feed. Examples of the vegetables includevegetable extracts, and the they are preferably contained in an amountof 1 to 30% in the feed. Examples of the vitamins include vitamin A, B1,B2, D and E, niacin, pantothenic acid and carotene, and the they arepreferably contained in an amount of 0.05 to 10% in the feed. Examplesof the minerals include calcium, phosphorus, sodium, potassium, iron,magnesium and zinc, and the they are preferably contained in an amountof 0.05 to 10% in the feed. Besides the above, a gelling agent, ashape-retaining agent, a pH adjustor, a seasoning, a preservative, anutritional supplement and the like which are commonly used in feed mayalso be contained.

[0059] The oil composition according to the present invention can beused in an oil-in-water type emulsion. A weight ratio of an oil phase toa water phase is 1/99 to 90/10, preferably 10/90 to 80/20, particularlypreferably 30/70 to 75/25. An emulsifier is preferably contained in anamount of 0.01 to 5%, particularly 0.05 to 3%. Examples of theemulsifier include various kinds of proteins such as egg proteins,soybean proteins, milk proteins, proteins separated from these proteinsand (partially) decomposed products of these proteins, sucrose fattyacid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fattyacid esters, glycerol fatty acid monoesters, polyglycerol fatty acidesters, polyglycerol condensed ricinoleic acid esters, glycerol organicacid fatty acid esters, propylene glycol fatty acid esters, lecithin andenzymatically decomposed lecithin. A stabilizer is preferably containedin an amount of 0 to 5%, particularly 0.01 to 2%. Examples of thestabilizer include thickening polysaccharides such as xanthan gum,gellan gum, guar gum, carrageenan, pectin, tragacanth gum and konjakmannan, and starch. A phytosterol is preferably contained in an amountof 0 to 10%, more preferably 1 to 7%, particularly preferably 2 to 5%.In addition, flavorings such as common salt, saccharides, vinegar, fruitjuices and seasoning, spicery such as spices and flavors, a colorant, apreservative, an antioxidant, etc. may be used. These raw materials maybe used to prepare oil-in-water type oil-containing foods such asmayonnaises, dressings, coffee whiteners, ice creams, whipped creams anddrinks in accordance with a method known per se in the art.

[0060] The oil composition according to the present invention can beused in a water-in-oil type emulsion. A weight ratio of a water phase toan oil phase is 85/15 to 1/99, preferably 80/20 to 10/90, particularlypreferably 70/30 to 35/65. An emulsifier is preferably contained in anamount of 0.01 to 5%, particularly 0.05 to 3%. Examples of theemulsifier include various kinds of proteins such as egg proteins,soybean proteins, milk proteins, proteins separated from these proteinsand (partially) decomposed products of these proteins, sucrose fattyacid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fattyacid esters, glycerol fatty acid monoesters, polyglycerol fatty acidesters, polyglycerol condensed ricinoleic acid esters, glycerol organicacid fatty acid esters, propylene glycol fatty acid esters, lecithin andenzymatically decomposed lecithin. A phytosterol is preferably containedin an amount of 0 to 10%, more preferably 1 to 7%, particularlypreferably 2 to 5%. In addition, flavorings such as common salt,saccharides, vinegar, fruit juices and seasoning, spicery such as spicesand flavors, a stabilizer such as a thickening polysaccharide or starch,a colorant, a preservative, an antioxidant, etc. may be used. These rawmaterials may be used to prepare water-in-oil type oil-containing foodssuch as margarine, margarine-like spreads and butter creams inaccordance with a method known per se in the art.

[0061] The oil composition according to the present invention can beused in portable oil-containing foods. The oil content in such a food ispreferably 1 to 30%, particularly preferably 1 to 20%. A phytosterol ispreferably contained in an amount of 0 to 20%, more preferably 1 to 20%,particulary preferably 2 to 15%. A saccharide such as sucrose, glucose,fructose, maltose, xylitol, sorbitol, erythritol or starch is preferablycontained in an amount of 40 to 99%. A carbonate foaming agent composedof an expanding agent such as sodium hydrogencarbonate and an acid agentsuch as tartaric acid, fumaric acid or citric acid is preferablycontained in an amount of 0 to 20%, particularly preferably 1 to 10%.These raw materials may be used to prepare portable oil-containing foodssuch as tablet confectionery, candy, caramel and gummy in accordancewith a method known per se in the art. In particular, the ability todissolve in a mouth is improved by the use of the carbonate foamingagent.

[0062] The oil composition according to the present invention can beused in bakery foods. The oil content in such a food is preferably 1 to40%, particularly preferably 5 to 35%. The content of a phytosterol ispreferably 0 to 20%, more preferably 1 to 20%, particularly preferably 1to 15%. The content of wheat flour is preferably 10 to 70%, particularlypreferably 20 to 60%. At least one of the whole egg, yolk, albumen,separated products thereof and decomposed products thereof is preferablycontained in an amount of 0 to 30%, particularly preferably 5 to 25%.Common salt is preferably contained in an amount of 0 to 2%,particularly preferably 0.1 to 1%. A saccharide and baking powder are ispreferably contained in amounts of 0 to 2.5% and 0 to 1%, respectively.These raw materials may be used to prepare bakery foods such as bread,cakes and cookies in accordance with a method known per se in the art.

[0063] Having generally described this invention, a furtherunderstanding can be obtained by reference to certain specific exampleswhich are provided herein for purposes of illustration only and are notintended to be limiting unless otherwise specified.

EXAMPLES Example 1

[0064] The following oil compositions were prepared.

[0065] Diglyceride Oil A:

[0066] Soybean oil fatty acid (650 parts by weight) and glycerol (107parts by weight) were subjected to esterification at 40° C. for 5 hoursunder 0.07 hPa using Lipozyme IM (product of Novo Nordisk Industry Co.).The enzyme was then separated by filtration, and the resultant filtratewas subjected to molecular distillation at 235° C. The distillate thusobtained was washed with water and then deodorized at 235° C. for 1 hourto obtain Diglyceride Oil A.

[0067] Diglyceride Oil B:

[0068] After a mixture of soybean oil fatty acid (455 parts by weight),the content of saturated fatty acids in which had been reduced bywinterization, rapeseed oil fatty acid (195 parts by weight) andglycerol (107 parts by weight) were subjected to esterification in thesame manner as in Diglyceride Oil A. The enzyme was then separated byfiltration, and the resultant filtrate was subjected to moleculardistillation at 235° C. The distillate thus obtained was washed withwater and then deodorized at 235° C. for 1 hour to obtain DiglycerideOil B.

[0069] Invention Products 1 to 3 and Comparative Products 1 to 3:

[0070] Diglyceride Oil A, Diglyceride Oil B, perilla oil (product ofOhota Yushi K.K.), rapeseed oil (product of Hohnen Co., Ltd.) were mixedat their corresponding weight ratios shown in Table 1. To the mixtures(each, 100 parts) were added vitamin E (MDE6000, product of Yashiro Co.,Ltd.; 0.1 parts), silicone (KS-66, product of Shin-Etsu Chemical Co.,Ltd.; 0.0002 parts) and citric acid (0.02 parts) to produce InventionProducts 1 to 3 and Comparative Products 1 to 3. Analytic results of theoil compositions thus obtained are shown in Table 1.

[0071] Invention Product 4 and Comparative Product 4:

[0072] Diglyceride Oil B, rapeseed oil and perilla oil were mixed attheir corresponding weight ratios shown in Table 3. To the mixtures(each, 100 parts) was added vitamin E (0.02 parts) to produce InventionProduct 4 and Comparative Product 4. Analytic results of the oilcompositions thus obtained are shown in Table 3.

[0073] Invention Product 5:

[0074] Diglyceride Oil B, rapeseed oil and linseed oil (product ofYoshihara Oil Mill, Ltd.) were mixed at its corresponding weight ratioshown in Table 3. To the mixture (100 parts) were added vitamin E (EOil-600, product of Riken Vitamin Co., Ltd.; 0.2 parts), vitamin Cpalmitate (Vitamin C Palmitate, product of Roche Co.; 0.025 parts) androsemary extract (Herbalox Type HT-O, product of Kalsec Co.; 0.025parts) to produce Invention Product 5. Analytic results of the oilcomposition thus obtained are shown in Table 3. TABLE 1 Inventionproduct Comparative product 1 2 3 1 2 3 Rapeseed oil 50 25 0 100 0 0Perilla oil 25 25 25 0 0 100 Diglyceride Oil A 0 0 75 0 100 0Diglyceride Oil B 25 50 0 0 0 0 Composition of glycerides*¹ TG 78 56.234.8 99.2 13 98.6 DG 21.9 43.7 65.1 0.7 86.9 1.3 1,3-DG 15.3 30.6 45.60.5 60.8 0.9 1,2-DG 6.6 13.1 19.5 0.2 26.1 0.4 MG 0.1 0.1 0.1 0.1 0.10.1 Composition of constitutive fatty acids*² Triglyceride C16:0 5 5 8 512 85 C18:0 2 2 3 2 4 3 C18:1 (ω9) 46 39 18 62 24 18 C18:2 (ω6) 19 20 2519 51 25 C18:3 (ω3) 25 31 45 8 6 45 Diglyceride C16:0 3 3 12 n.t. 12 8C18:0 1 1 4 n.t. 4 3 C18:1 (ω9) 38 38 24 n.t. 24 18 C18:2 (ω6) 48 48 51n.t. 51 25 C18:3 (ω3) 8 8 6 n.t. 6 45

Example 2 Repeated Test on Frying

[0075] Each of the oil compositions (Invention Products 1 to 3 andComparative Products 1 to 3) prepared in Example 1 was used torepeatedly fry freezed vegetable croquettes. The acid value and coloringof each oil composition in the course of the frying, and the flavor ofthe cooked products were evaluated.

[0076] (Cooking Conditions)

[0077] Material of fry: Freezed vegetable croquettes (product ofAjinomono Co., Ltd.).

[0078] Amount of oil: 1500 g; No additional oil was supplied in thecourse of the frying.

[0079] Fryer: Electric fryer (NF-F150, manufactured by MatsushitaElectric Industrial Co., Ltd.) was used.

[0080] Oil temperature: 190° C.

[0081] Frying conditions:

[0082] A croquette (about 75 g) was fried over 5 minutes once every 15minutes. After 2 minutes from the beginning of the frying, the croquettein the oil composition was turned from side to side. This fryingoperation was repeated 40 times (cumulative frying time: 10 hours).

[0083] (Acid Value of Oil Composition)

[0084] A part of the oil composition in the course of the frying wastaken out every 2 hours to determine its acid value (Standard oils andfats analyzing test method 2.3.1-1996 (The Japan Oil Chemists'Society)). The value was expressed as a relative value that a valuebefore the frying is regarded as 1.

[0085] (Coloring of Oil Composition)

[0086] A part of the oil composition in the course of the frying wastaken out every 2 hours to measure its redness (R) and yellowness (Y) inaccordance with the Lovibond method (Standard oils and fats analyzingtest method 2.2.1.1-1996 (The Japan Oil Chemists' Society): instrumentused; Lovibond PFX880 Tintometer, using 1-inch glass cell), therebyfinding a calculated value (10R+Y) thereof.

[0087] In addition, the oil composition after 10 hours from thebeginning of the frying and a cooked product fried at this time wereevaluated by 10 panelists in accordance with the following evaluationstandards.

[0088] (Flavor of Oil Composition)

[0089] A: Far excellent because no unpleasant taste such as acid orastringent taste was observed;

[0090] B: Excellent because an unpleasant taste was scarcely observed;

[0091] C: An unpleasant taste such as acid or astringent taste wassomewhat observed;

[0092] D: Poor flavor because an unpleasant taste was observed.

[0093] (Flavor of Cooked Product)

[0094] A: Far excellent because no unpleasant taste such as acid orastringent taste was observed;

[0095] B: Excellent because an unpleasant taste was scarcely observed;

[0096] C: An unpleasant taste such as acid or astringent taste wassomewhat observed;

[0097] D: Poor flavor because an unpleasant taste was observed. TABLE 2Properties of frying oil Acid value Color (10R + Y) Flavor After AfterAfter After After After After After After After Oil Cooked 2 hrs 4 hrs 6hrs 8 hrs 10 hrs 2 hrs 4 hrs 6 hrs 8 hrs 10 hrs compn. product Invention1.3 2.0 2.7 4.0 5.5 43 62 120 190 203 A A Product 1 Invention 1.3 2.12.8 4.1 5.6 44 64 139 254 271 A A Product 2 Invention 1.3 2.2 2.9 4.36.0 44 65 152 285 310 B B Product 3 Comparative 1.3 2.1 2.8 4.0 5.4 4260  79 101 182 A A product 1 Comparative 1.5 2.5 3.3 4.7 6.5 45 75 208505 780 C C product 2 Comparative 1.5* — — — —  74* — — — — D* D*product 3

[0098] All the oil compositions (Invention Products 1 to 3) according tothe present invention scarcely underwent deterioration compared with thehigh diglyceride-containing oil (Comparative Product 2) and perilla oil(Comparative Product 3), and the flavor of the products cooked by usingthem was also good. In particular, the coloring of the oil compositionsduring the frying was markedly prevented. As described above, the oilcompositions according to the present invention were good in flavor,hard to be colored and high in hydrolytic stability and the like evenunder severe conditions that heating was performed at a high temperaturefor a long period of time, and thus excellent in suitability for frying.

Example 3 Administration Test to Human

[0099] (Test Sample)

[0100] Comparative Product 4 and Invention Product 4 prepared in Example1 were used as test samples.

[0101] An oil-in-water type emulsified drink prepared so as to give anoil content of 10% was used upon ingestion of each test sample. Thecomposition thereof is shown in Table 4. The drink obtained by usingInvention Product 4 was good in flavor, appearance, emulsion stability,etc. The oil composition according to the present invention was able tobe satisfactorily used in the application field of oil-in-water typeemulsions. TABLE 3 Invention Comparative Invention Product 4 Product 4Product 5 Rapeseed oil 31.4 81.4 30 Perilla oil 18.6 18.6 0 linseed oil0 0 20 Diglyceride Oil B 50 0 50 Composition of glycerides*¹ TG 56.299.3 55.9 DG 43.7 0.6 43.5 1,3-DG 30.6 0.4 30.5 1,2-DG 13.1 0.2 13.0 MG0.1 0.1 0.6 Composition of constitutive fatty acids*² Triglyceride C16:05 5 5 C18:0 2 2 2 C18:1 (ω9) 44 53 43 C18:2 (ω6) 21 18 23 C18:3 (ω3) 2518 27 Diglyceride C16:0 3 n.t. 3 C18:0 1 n.t. 1 C18:1 (ω9) 38 n.t. 39C18:2 (ω6) 48 n.t. 47 C18:3 (ω3) 8 n.t. 9

[0102] TABLE 4 Formulation of test drink % Oil 10 Water 47.8 SeasoningTORYS CONC (product of Suntory Limited) 25 Reducing starch hydrolyzatePO-300 (product of 6.44 Towa Chemical Industry, Co., Ltd.) Reducingstarch hydrolyzate PO-500 (product of 6.44 Towa Chemical Industry, Co.,Ltd.) Erythritol 3.32 Emulsifier Polyglycerol SY Glyster MS-500 (productof 1 Sakamoto Yakuhin Kogyo Co., Ltd.)

[0103] The above materials other than the oil were mixed and heated to60° C. into a solution. The oil heated to 60° C. was added to thesolution and emulsified by means of T.K. homomixer (product of TOKUSHUKIKA KOGYO CO., LTD.) at 6000 rpm. The emulsion was then treated byhomogenizer (product of SANWA MACHINE CO., INC.) at 200 Kgf/cm² (2 pass)to prepare an emulsified drink.

[0104] (Subject and Testing Method)

[0105] This test was performed with sufficient consideration accordingto the sprit of Helsinki Declaration. The subjects were 16 healthy menaged 27 to 44 years. The ingestion time, contents and amount of a supperin the day before the test were unified as to all the subjects.Ingestion of other foods and drinks than water was forbidden from theingestion of the supper to the beginning of the test at the day afterthe supper.

[0106] In the test, the test drink was ingested in an amount sufficientto give a lipid of 10 g per 60 kg of body weight to collect blood beforethe ingestion and after 3, 4 and 5 hours from the ingestion. The testprescribed that the subjects keep quiet during the test, and ingestionof other foods and drinks than water are forbidden.

[0107] An crossover test was carried out as to the 2 test samples inaccordance with the above-described method.

[0108] (Analysis of Blood)

[0109] The blood samples collected were used to evaluate the behavior ofserum lipids after the ingestion of the test samples. More specifically,serum neutral lipid after the ingestion of each test sample andchylomicron TG that is a lipoprotein lipid formed in the blood fromlipids absorbed through a small intestine were determined.

[0110] The value of the serum neutral lipid after the ingestion of thetest sample is shown in Table 5 as a rate of change (%) of the serumneutral lipid value regarding a value before the ingestion of the lipidas 100. A significance test was conducted by the paired-t test. As aresult, the invention product was found to have an effect ofsignificantly inhibiting the increase of serum neutral lipid after 3hours from the ingestion of the test sample compared with thecomparative product (level of significance p<0.05). TABLE 5 Rate (%) ofchange of serum neutral lipid value after ingestion of test sampleBefore After 3 After 4 After 5 ingestion hours hours hours Comparative100 156 ± 7  136 ± 7 109 ± 5 Product 4 Invention 100 139 ± 7* 132 ± 5119 ± 3 Product 4

[0111] The results as to chylomicron TG after the ingestion of the testsamples are shown in Table 6. The paired-t test was performed likewise.As a result, the invention product was found to have an effect ofsignificantly inhibiting the increase of chylomicron TG after 3 hoursfrom the ingestion of the test sample (level of significance p<0.05).TABLE 6 Chylomicron TG (mg/dl) after ingestion of test sample BeforeAfter 3 After 4 ingestion hours hours Comparative 3 ± 1 21 ± 4  11 ± 3Product 4 Invention 3 ± 1 15 ± 2* 10 ± 2 Product 4

[0112] The oil composition (Invention Product 4) according to thepresent invention inhibited the increase of chylomicron TG formed fromlipids absorbed through a small intestine, thereby significantlyinhibiting the increase of serum neutral lipid after eating.

Example 4 Soft Capsule

[0113] DHA 22 (product of MARUHA CORP.; 40 parts by weight), corn oil(10 parts by weight), catechin (0.2 parts by weight) and tocopherol(0.05 parts by weight) were mixed with Diglyceride Oil A (50 parts byweight) described in Example 1 to prepare an oil composition (InventionProduct 6). This composition (300 mg) was encapsulated into a softcapsule body in an oval form to formulate a soft capsule preparation.

Example 5 Frizzled Bean Sprouts

[0114] The oil composition (Invention Product 3; 8 parts by weight)prepared in Example 1 was placed on a frying pan (24 cm), and the fryingpan was heated by a gas heater. After 30 seconds, bean sprouts (200parts by weight) were placed on the frying pan and frizzled for 30seconds. Common salt (1.4 parts by weight) was then added, and the beansprouts were further frizzled for 30 seconds to cook frizzled beansprouts. The frizzled bean sprouts thus obtained were good in all offlavor, appearance and operability upon cooking. The oil compositionaccording to the present invention was able to be satisfactorily used inthe application field of frizzled foods.

Example 6 Chinese Dressing (Separation Type)

[0115] (parts by weight) Oil composition (Invention Product 1) 25 Sesameoil 5 Soy sauce 25 Vinegar (acid content: 10%) 11 Japanese wine 6Refined sucrose 3 Common salt 1.4 Oyster sauce 0.2 Sodium glutamate 0.15Chinese bouillon (powder) 0.1 Garlic oil 0.02 Ginger oil 0.01 Water23.12

[0116] After the components other than the oil composition and sesameoil were mixed with one another, the oil composition and sesame oil wereadded to prepare a Chinese dressing (separation type). The Chinesedressing (separation type) thus obtained was good in both flavor andappearance. The oil composition according to the present invention wasable to be satisfactorily used in the application field of dressings.

Example 7 Short Bread

[0117] (parts by weight) Oil composition (Invention Product 4) 200 Weakflour 350 Strong flour 150 Refined sucrose 150 Whole egg 125 Common salt2.5

[0118] Refined sucrose and common salt were placed in a bowl and stirredby a Hobart mixer. The whole egg was gradually added to the mixture, andstirring was conducted again by the Hobort mixer. A mixture of weakflour and strong flour prepared in advance was added in 3 portions, andthe resultant mixture was further stirred by the Hobart mixer. A doughthus prepared was divided into small portions (each, 25 g), and eachportion was put into a metal frame. The portion was baked in an oven(160° C., 50 minutes), removed from the frame and allowed to cool downto prepare short breads. The short breads thus obtained were good inboth flavor and appearance. The oil composition according to the presentinvention was able to be satisfactorily used in the application field ofbakery foods.

Example 8 Margarine-Like Spread

[0119] (Oil phase) (parts by weight) Oil composition (Invention Product2) 33.38 Hardened palm oil (IV = 2) 4 Hardened soybean oil (IV = 43) 2Monoglyceride 0.5 Lecithin 0.5 Polyglycerol condensed 0.5 ricinolic acidester Flavor 0.1 Vitamin E 0.02

[0120] (Water phase) (parts by weight) Distilled water 57.4 Nonfat drymilk 0.3 Common salt 1.3

[0121] The above oil phase and water phase were separately prepared andthen mixed and emulsified by a homomixer. The emulsion thus obtained wasquenched and plasticized by a method known per se in the art, therebypreparing a margarine-like spread. The margarine-like spread thusobtained was good in all of flavor, appearance and emulsion stability.The oil composition according to the present invention was able to besatisfactorily used in the application field of water-in-oil typeemulsions.

Example 9 Oxidation Stability Test

[0122] Invention Product 5 prepared in Example 1 was used as a sample toevaluate it as to oxidation stability in accordance with the standardoils and fats analyzing test method 2.5.1.2-1996 (edited by The JapanOil Chemists' Society). As a result, the Rancimat induction time ofInvention Product 5 was 4.6 hours, and it was hence found that the oilcomposition has good oxidation stability.

Example 10 Fried Food (Tempura)

[0123] Invention Product 5 prepared in Example 1 was used to cooktempura under the following conditions.

[0124] Amount of oil: 600 g (Chinese pan).

[0125] Oil temperature: 180° C., heated (medium fire) by a gas heater.

[0126] Material:

[0127] eight prawns (black tiger),

[0128] eight pieces of lotus root

[0129] eight pieces of pumpkin

[0130] eight pieces of pimento (cut into halves) and eight pieces ofeggplant (cut into halves).

[0131] Coating of tempura:

[0132] wheat flour (100 g)

[0133] egg (50 g) and

[0134] water (150 g).

[0135] The tempura thus obtained was good in both flavor and appearance.The oil composition after the cooking of tempura was also good likewise.The oil composition according to the present invention was able to besatisfactorily used in the application field of fried foods.

Example 11 Emulsion Stability Test

[0136] The oil compositions (Invention Product 1, Comparative Product 1and Comparative Product 2) prepared in Example 1 were used to prepareoil-in-water type emulsified drinks in accordance with theircorresponding formulations shown in Table 4. The emulsified drinks thusobtained were respectively charged into 50-ml glass-made samplingbottles and hermetically sealed. After the bottles were left at rest at20° C. for a week, the emulsified state of each drink was visuallyobserved. The results thereof are shown in Table 7. TABLE 7 Right afterAfter 1 week Oil composition emulsification at 20° C. Invention Product1 A A Comparative Product 1 A A Comparative Product 2 A D

[0137] A: Emulsion was very stable because neither oil off norseparation of water was observed;

[0138] B: Emulsion was stable because oil off and separation of waterwere scarcely observed;

[0139] C: Emulsion was somewhat unstable because oil off and separationof water were observed;

[0140] D: Emulsion was unstable because separation occurred.

[0141] It was found that the emulsified drink using Invention Product 1has good emulsion stability.

Example 12 Animal Test

[0142] Feed B (comparative) obtained by adding triglyceride (TAG; 6%) toa composition based on a high-fat and high-sucrose feed shown in Table 8was given to a control group, and Feed C (comparative) obtained byadding diglyceride (DAG; 6%) in place of TAG (6%) or Feed A (invention)obtained by adding DAG (3%) and linseed oil (3%) was given to a testgroup and freely ingested (in each group, n=10). Changes of increase inbody weight and increase in body weight per calorie after breeding for 8weeks are shown in Table 9. TABLE 8 Component of feed Feed A Feed B FeedC (wt. %) (invention) (comparative) (comparative) linseed oil*¹ 3 0 0DAG*² 3 0 6 TAG*³ 0 6 0 Fat*⁴ 24 24 24 Sucrose 13 13 13 Casein 20 20 20Cellulose 4 4 4 Mineral mixture*⁵ 3.5 3.5 3.5 Vitamin mixture*⁶ 1 1 1Potato starch 28.5 28.5 28.5

[0143] TABLE 9 Body weight Increase Increase in After 8 in body weightbody weight Feed Initial (g) weeks (g) (g) (g/cal) A (invention) 23.4 ±1.1 31.3 ± 2.2 8.0 ± 2.0 10.1 ± 2.5 B (comparative) 23.4 ± 0.8 33.4 ±3.1 10.0 ± 3.0  12.3 ± 3.8 C (comparative) 23.4 ± 1.4 32.3 ± 1.6 8.9 ±1.6 11.5 ± 2.1

[0144] It was clearly known that when Feed A according to the presentinvention was ingested, increase in body weight and increase in bodyweight per calorie are inhibited. The oil composition according to thepresent invention was able to be satisfactorily used in the applicationfield of feeds.

[0145] As described above, the oil compositions according to the presentinvention are mixed oils composed of triglycerides containing a greatamount of ω3 type unsaturated fatty acids among constitutive fatty acidsin glycerides and diglycerides containing a small amount of the ω3 typeunsaturated fatty acids and thus are good in flavor, hard to be colored,excellent in hydrolysis stability and resistance to oxidation, good inemulsion stability and excellent in intake balance among fatty acidseven under severe conditions that heating is performed at a hightemperature for a long period of time, can be widely developed tomedicinal preparations and foods and moreover exhibit an excellentinhibitory effect on accumulation of body fat by ingestion of a smallamount of diglycerides.

1. An oil composition comprising the following components (A) and (B):(A) 15 to 70% by weight of diglycerides in which less than 15% by weightof the constitutive fatty acids are ω3 type unsaturated fatty acids; and(B) 30 to 85% by weight of a triglyceride in which at least 15% byweight of the constitutive fatty acids are ω3 type unsaturated fattyacids.
 2. The oil composition according to claim 1, wherein among the ω3type unsaturated fatty acids in the component (B), α-linolenic acid iscontained in an amount of at least 50% by weight.
 3. The oil compositionaccording to claim 1 or 2, which further comprises 0.004 to 5% by weightof an antioxidant.
 4. The oil composition according to any one of claims1 to 3, which further comprises 0.02 to 0.5% by weight of acrystallization inhibitor.
 5. The oil composition according to any oneof claims 1 to 4, which further comprises at least 0.05% by weight of aphytosterol.
 6. A food comprising the oil composition according to anyone of claims 1 to
 5. 7. A feed comprising the oil composition accordingto any one of claims 1 to
 5. 8. A pharmaceutical comprising the oilcomposition according to any one of claims 1 to
 5. 9. A cooking oilcomprising the oil composition according to any one of claims 1 to 5.10. The food according to claim 6, wherein said food is an oil-in-watertype oil-containing food.
 11. The food according to claim 6, whereinsaid food is a water-in-oil type oil-containing food.
 12. The foodaccording to claim 6, wherein said food is a portable oil-containingfood.
 13. The food according to claim 6, wherein said food is a bakeryfood.